(+-)-8-Cyano-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one

Base Information

• Chemical Name: (+-)-8-Cyano-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one
• CAS No.: 104107-08-6
• Molecular Formula: C13H11N3O
• Molecular Weight: 225.2459
• Mol file: 104107-08-6.mol

Synonyms:Benzo(h)cinnolin-8-carbonitrile, 2,3,4,4a,5,6-hexahydro-3-oxo-, (+-)-;(+-)-2,3,4,4a,5,6-Hexahydro-3-oxobenzo(h)cinnolin-8-carbonitrile;Benzo(h)cinnoline-8-carbonitrile, 2,3,4,4a,5,6-hexahydro-3-oxo-, (+-)-;

Chemical Property of (+-)-8-Cyano-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.4g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+-)-8-Cyano-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one

There total 10 articles about (+-)-8-Cyano-4,4a,5,6-tetrahydrobenzo(h)cinnolin-3(2H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 24.0%

6-cyano-1-oxo-1,2,3,4-tetrahydronaphth-2-yl acetic acid (104107-34-8) → 8-cyano-4,4a,5,6-tetrahydrobenzocinnolin-3<2H>-one (104107-08-6,121866-02-2)

Guidance literature:

With hydrazine hydrate; In acetic acid; Heating;

DOI:10.1016/0223-5234(90)90196-A

Reference yield:

6-acetamido-1,2,3,4-tetrahydronaphthalen-1-one (88611-67-0) → 8-cyano-4,4a,5,6-tetrahydrobenzocinnolin-3<2H>-one (104107-08-6,121866-02-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaOH / H₂O / 3 h / Ambient temperature

2: 71 percent / Zn, AcOH / H₂O / 0.5 h / 100 °C

3: 91 percent / H₂NNH₂*H₂O / ethanol / 3 h / Heating

4: 85 percent / 4 N HCl / 2 h / 100 °C

5: 1) NaNO₂, conc. HCl, 2) Na₂CO₃, CuCN / 1) H₂O, 2) H₂O, Et₂O, 50 deg C, 1 h

With hydrogenchloride; sodium hydroxide; sodium carbonate; hydrazine hydrate; acetic acid; zinc; sodium nitrite; In ethanol; water;

DOI:10.1021/jm00130a009

Reference yield:

6-(acetylamino)-1,2,3,4-tetrahydro-1-oxo-2-naphthalenideneacetic acid (103602-85-3) → 8-cyano-4,4a,5,6-tetrahydrobenzocinnolin-3<2H>-one (104107-08-6,121866-02-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / Zn, AcOH / H₂O / 0.5 h / 100 °C

2: 91 percent / H₂NNH₂*H₂O / ethanol / 3 h / Heating

3: 85 percent / 4 N HCl / 2 h / 100 °C

4: 1) NaNO₂, conc. HCl, 2) Na₂CO₃, CuCN / 1) H₂O, 2) H₂O, Et₂O, 50 deg C, 1 h

With hydrogenchloride; sodium carbonate; hydrazine hydrate; acetic acid; zinc; sodium nitrite; In ethanol; water;

DOI:10.1021/jm00130a009

upstream raw materials:

6-cyano-1-oxo-1,2,3,4-tetrahydronaphth-2-yl acetic acid

potassium cyanide

dl-8-amino-4,4a,5,6-tetrahydro-2H-benzo(h)-cinnolin-3-one

8-Acetylamino-4,4a,5,6-tetrahydrobenzocinnolin-3(2H)-one